N-bromobutanimide → 5-((4-Bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid

HRID 928971Notes

Reaction equation

HRID 928971 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:10]([C:19]([OH:21])=[O:20])=[CH:11][C:12]2[O:16][CH:15]=[N:14][C:13]=2[C:17]=1[F:18].C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C>[Br:29][C:6]1[CH:5]=[CH:4][C:3]([NH:8][C:9]2[C:10]([C:19]([OH:21])=[O:20])=[CH:11][C:12]3[O:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 897047945-((2-Chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid

Product 1

HCID 897048215-((4-Bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acidYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-((2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid (12.31 g, 40.14 mmol) in DMF (100 mL) was added NBS (7.86 g, 44.15 mmol). After stirring for 4 h at ambient temperature, the reaction was quenched by water and the precipitate was filtered. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 50:1, v/v) and gave the desired product (pale brown solid, 10.82 g, 69.9% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.08 (s, 1H), 9.42 (s, 1H), 8.96 (s, 1H), 8.27 (s, 1H), 7.82 (d, J=12.0 Hz, 1H), 7.37 (m, 1H), 6.65 (m, 1H).

Workup

  1. customthe reaction was quenched by water
  2. filtrationthe precipitate was filtered
  3. customThe crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 50:1

Sources & evidence

ORD record
ord-409ab09f4eb241f58cbdbe469ec82d5b
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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